Sc(OTf)3-Catalyzed Reaction of Purines with o-Hydroxybenzyl Alcohols for Construction of Acyclic Nucleosides

Efficient alkylation of purines with ortho-hydroxybenzyl alcohols under mild condition has been achieved by Sc(OTf)(3) catalysis. This C-N bond formation process is proposed to proceed through an ortho-quinone methide intermediate. The reaction allows for efficient synthesis of various acyclic nucleoside analogs, with excellent yields of up to 96%, across a broad range of substrates and the yields were maintained as the reactions were scaled up.

Automated summary

Efficient alkylation of purines with ortho-hydroxybenzyl alcohols under mild condition has been achieved by Sc(OTf)(3) catalysis, leading to the formation of various acyclic nucleoside analogs with excellent yields of up to 96% and maintained yields as reactions were scaled up.